


Double Dare

by Threshie



Category: Supernatural
Genre: Beer, Bisexual Dean Winchester, Bisexual Sam Winchester, Caring Sam, Castiel In Love, Castiel in the Bunker, Couch, Dare, Destiel - Freeform, Drunken Kissing, Fluff, Fluff and Angst, Flustered Dean, M/M, Men of Letters Bunker, Non-Smut, Pining, Polyamory, Sastiel - Freeform, Team Free Will, WinCasWin
Language: English
Status: Completed
Published: 2017-03-19
Updated: 2017-05-06
Packaged: 2018-10-07 16:10:11
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 6,880
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10364370
Author URL: https://archiveofourown.org/users/Threshie/pseuds/Threshie
Summary: Team Free Will have a few beers, and the brothers discover that everybody there but Cas has kissed a guy before.





	1. Kisses

Castiel couldn't get drunk. Not without drinking the whole liquor store, anyway. Drinking beer seemed to be more of a social gesture to Sam and Dean, though, so he joined them when they offered. The three sat on the small overstuffed couch that Dean had acquired for the bunker a few weeks ago, beers in hand and nothing to do but talk to each other. 

“Maybe next we should get a TV,” Dean commented dryly, toasting to the empty spot on the wall in front of them. They were more than a few beers in at this point, and he and Sam were definitely acting differently. The older Winchester draped an arm over Castiel's shoulders, smirking at him. “You could study up on the pizza man again, Cas.” 

The angel looked at him dubiously, taking a sip of his beer. 

“That was years ago, Dean. I am surprised you remember that.”

Dean snorted, sipping his beer as well. 

“Angel hangs around in the living room watching pornos, smooches a demon later with what he learned. How could I forget?”

“I vote for getting a bigger couch before the TV,” Sam commented from Cas's other side, shifting on the seat. They were elbow to elbow on the couch, and for someone as tall as Sam it had to feel even more cramped. Cas glanced his way, offering a sympathetic nod. He'd rather not think about Meg and how unstable he'd been at the time of that kiss, so the subject change was welcome.

Dean seemed to disagree, though. 

“Most people learn to kiss the clumsy, embarrassing way,” he commented, leaned forward to look at his brother around Castiel. “Like you and Amy Reiner, right Sammy?”

“Shut up,” Sam shot back, shaking his head and doing that disbelieving little laugh he did when he was flustered. Cas had always found that endearing.

“Who did you learn to kiss with, Dean?” Cas turned back to him. Why was it a surprise that he was so close, when his arm was still around the angel's shoulders? Cas blinked and took a sip of his beer, watching curiously as Dean's cheeks turned pink and his green eyes got all shifty. His freckles stood out starkly with the blushing. 

“Uh. Can't really remember,” he said, swigging his beer. 

“Even I can tell that you're lying,” Cas informed him, leaning back against the couch. He caught Sam nodding out of the corner of his eye. 

“I thought you said it was Becky Harrison.”

“That was the first...” Dean trailed off, mumbling the rest and fidgeting. Alcohol was such an odd thing. Dean probably would have easily lied while sober, but at the moment he was an open book — and this Becky Harrison was definitely not the first person he had ever kissed.

Sam blinked and sat up, surprised he'd been wrong about something he thought he knew about his brother.

“C'mon, who was it?” He gestured to Castiel. “It's not like we're gonna tell anybody, Dean.” The angel exchanged a glance with him and nodded solemnly. 

“Yes. We'll keep your secret.” 

Dean just looked sheepish now. He finally moved his arm from Cas's shoulders to run a hand through his hair, clearing his throat.

“Becky was the first GIRL I kissed.” 

Sam opened his mouth to speak, and was promptly interrupted. 

“It's not what you think! I'm not gay. I've been with tons of girls!”

“That's...uh, that's not what I was going to say,” Sam replied awkwardly, rotating the beer bottle in his hands and focusing on it. He took a deep breath. “I-I'm just surprised, I mean, I thought you'd freak out so I never TOLD you, but...”

Dean was looking pretty freaked out right now, and was staring at his brother.

“Whoa, hold on. You're gay?”

“No, no,” Sam said hastily, holding up a hand. He blushed and admitted more quietly, “Bi.”

After a long, stunned silence from Dean (while Cas tried to come up with what he could possibly say to add to this conversation in any meaningful way), Sam continued shyly, “I-I messed around with a few guys in college. And I kissed a guy at a party.” Visibly mustering courage, he added, “How about you? Was the first kiss the only time it was a guy?”

Cas turned back to watch Dean, curious what answer he'd give. The staring only seemed to make him uncomfortable, though. The green-eyed man focused on his beer bottle like Sam had, replying a bit too hastily, “Yes. Now let's drop it, okay? Next Cas is gonna tell me HE'S kissed a guy.” 

“I've only kissed women,” Castiel assured him, patting his shoulder. “Though kissing a man can't be much different. Human mouths are fairly similar.” He paused and looked at Dean's lips thoughtfully.

“Yeah, well Dean's never kissed a man,” Sam pointed out, and now it was his turn to drape an arm around Castiel's shoulders (mostly to be able to lean closer to talk to Dean. Probably.) “Sounds like that kiss was with another kid back when you were little.”

Dean huffed and took another swig of his beer, blushing. Cas had never seen him blush so much, and it was endearing. 

“Cas's right, how different can it be?”

Sam looked down at Cas, who was just inches away with how the taller man was leaned against him, and smiled sweetly. 

“Why don't you kiss him and find out?”

“Kiss Cas? C'mon!” Dean sputtered, gesturing to them like that was ridiculous. “He'd PROBABLY mind!”

“I wouldn't mind,” Castiel told him honestly, turning away from Sam to meet his eyes. Determined, he added, “Then I would know what it was like to kiss a man as well.” 

Sam sat up and gave Cas's shoulder a small push, chuckling. 

“I dare you, Dean.”

“What are we, eight?” Dean grumbled, sitting his empty beer bottle on the floor beside the couch. He turned to Cas, though, looking thoughtful. “...I'll do it, but it's a double dare.”

The angel blinked, glancing at Sam quickly when the taller man groaned. 

“Are you serious?”

“Hell yes I am,” Dean said firmly, scooting closer to Castiel. That pressed both of the brothers against the angel's sides, and rather than feeling crowded, he actually kind of liked it. “You have to kiss him, too.”

Feeling the challenging stare exchanged between the two, Cas sipped his beer and tried to act nonchalant. Being kissed by either of the Winchesters seemed like a good thing. He had only kissed a person before, too, not had them kiss him. This would be interesting.

Sam sat his beer aside on the floor.

“Fine. But you go first.”

“You're gonna regret that,” Dean said, smirking as he turned to Cas. “I'm a tough act to follow!” 

The angel was beginning to wonder if this was a good idea. Sam and Dean were drunk. They would probably regret this tomorrow. Sam took the beer out of his hand carefully, though, and then Dean was cupping his face in both hands. 

“Dean, maybe—” Whatever he was about to say was forgotten the moment Dean pressed their lips together. Being kissed was nothing like kissing someone else — there was a strange satisfaction in being pressed into the plush couch cushions. It was not a chaste kiss, either. For the amount of blushing he had been doing a moment ago, Dean was not shy about this. 

After what felt like an eternity of very enjoyable sensations and tasting the beer on each other's tongues, Dean abruptly sat back and patted Castiel's shoulders, blushing furiously. 

“Wow, uh, g-got kinda carried away. Sorry, Cas,” he said, flustered.

“It's okay,” the angel replied, still dazed from the kissing itself. So far, in his very limited experience, being kissed by a man was much better than kissing a woman. Or maybe that was just being kissed by Dean? 

Remembering that this was a double dare, he finally snapped out of it and turned to see what Sam was doing. The taller man looked pretty surprised at his brother's enthusiasm. Dean was competitive, but he had to have liked the kiss to be that flustered afterward, right? It had seemed like a very good kiss to Cas, so it was probably enjoyable for Dean was well.

“Guess it's my turn,” Sam told the angel, meeting his eyes worriedly. “You still okay with this, Cas? You don't have to do it just because we made some stupid bet. Really, it's okay.”

Castiel's gaze drifted from his hazel eyes down to his mouth. Sam's lips looked soft. He probably kissed more gently than Dean, maybe. He had to admit that he wanted to find out.

Feeling his face heat up, he imagined that he must look all pink like Dean did right now. 

“I am still okay, Sam,” he assured the brunette. Sam smiled at that, the worry still obvious with how his brows furrowed. He brought a hand up to cup the angel's face, turning it toward him and leaning down. 

“Okay,” he whispered.

His lips were indeed soft, Castiel thought, one hand moving instinctively to grip the front of Sam's t-shirt. And this kiss was nothing like the passionate one from Dean. It was very gentle, slower, and instead of pressing Cas against the couch, Sam pulled him close to his chest. It was different to be kissed by someone so much taller, too — Cas found that he had to tilt his head back.

Like his brother, Sam was quite invested in this dare, and he only broke the kiss when both of them were out of breath. Loosening his arms around the angel's waist, the brunette sat back a little to give him some space. Castiel stared at up at him, blushing faintly. 

The most common thing the two kisses had was the taste of the beer they'd all been drinking. Other than that, the two brothers were like night and day in their approach to this. They weren't going to make him choose which kiss was better, were they? How could he possibly decide?

“So, who won?” Dean spoke up, as if reading his mind. 

“It's a dare, not a competition,” Sam said, before Cas could reply. The angel fidgeted as both of the brothers went to put an arm around his shoulders at the same time, and their hands bumped instead. 

“Er. Yes,” he agreed with Sam. “You are both much better at this than I am.” He was starting to dread the morning. Not only would the brothers most likely be hung over, but they might just be angry at him — the one sober person present — for allowing them to do this. It wasn't as if he'd asked them to, but all the same...

Dean, he noted, had settled for resting his arm along the back of the couch. A glance told him that Sam had done the same. Having both of their arms around him wouldn't have been a problem. One could have gone around his waist and the other around his shoulders. He decided not to mention it, though; they'd be in bad enough moods tomorrow as it was.

And he would have all night to sit awake and remember those kisses.

**Notes for the Chapter:**

> Some fluffy silliness.


	2. Coffee

Usually Sam made the coffee each morning, but Castiel had learned how to use the machine by now. He decided that it might be kind to have a pot ready for the brothers to drink when they woke up with inevitable hangovers. Sure enough, just a few minutes after the warm roasted scent started drifting through the bunker, Dean came wandering into the kitchen. 

Castiel smiled at him and offered him a cup of coffee.

“Good morning, Dean.”

The green eyed man took the cup automatically, looking groggy. He'd slept in his clothes – jeans and a flannel shirt over a tank top – and his hair was a mess, but that didn't make him any less attractive, Cas thought fondly. The imperfect mortality was part of what made humanity so wonderful.

“Hey,” Dean greeted, lifting the coffee mug in a little toast before going to take a sip. He stopped short, though, and frowned at his hand. 

The parade of confusion, disbelief and dismay that crossed his expression in the next minute was fascinating to observe. Did he not remember last night before that moment? Maybe toasting with the coffee made him remember toasting the wall with his beer.

“Dean,” Cas began, meaning to reassure him. Dean cut him off, though, staring at him uneasily.

“Cas, did we get drunk last night?”

The angel nodded quickly. 

“You and Sam did, yes. I would need many more beers for–“

“Whoa. Hold up.” Dean sat his coffee down, wincing slightly from his own raised voice. Right, being hung over caused headaches. “Did we — uh, wh-what exactly did we talk about, Cas? When we were drunk?”

Castiel tilted his head, trying to decide if he was supposed to believe Dean didn't remember. Clearly he did, but judging by the uneasy look and the way his face was flushing, he didn't want to admit to it. Cas's staring wasn't helping — he just got more and more uncomfortable, and finally took a big swig of his coffee to try and cover it up. 

That coffee was hot. Dean's face said he'd just realized that, but he stubbornly swallowed it anyway, coughing a bit and pretending his eyes weren't watering. In return, Cas tried not to look amused.

“You don't remember?” He asked innocently.

Dean's gaze moved to meet the angel's eyes, and Cas saw a flash of panic before he quickly looked back down at his cup. 

“Uh. Well, yeah, sort of, but I-I could've imagined some parts, I mean, we were pretty drunk, who knows,” he said all in a jumble, sounding more like he was trying to convince himself than Castiel. With every word, he was getting more flustered. It was strangely attractive, in a comical way. Dean was usually so confident.

“We talked about kissing,” Cas told him honestly, pouring himself a cup of coffee as well. As far as talking went, that WAS just about the whole story of what they'd said. He turned and looked at Dean thoughtfully, sipping the coffee. 

Squirming under his intent gaze, the older Winchester ran a hand through his messy hair, glancing around the kitchen. 

“Right. Right, I remember that,” he admitted uncomfortably, turning to lean back against the counter. 

“Then Sam dared you to kiss me, and you dared him to do the same,” Cas added mildly, leaning on the counter too. “And we didn't do much talking after that.”

The groan from Dean was a bit alarming. Cas glanced to see the brunette with a hand pressed over his face.

“That really happened? Oh, shit...” Though Castiel couldn't see his face, there was a radiating aura of embarrassment coming from that whole side of the kitchen. Sympathetically, the angel stepped closer and retrieved the coffee mug from his hand, because he'd forgotten it and was dangerously close to spilling it. 

“It did. I'm sorry – I probably shouldn't have allowed it,” he admitted guiltily, “but it made you and Sam happy, and I don't see you happy very much.” He hadn't exactly been unhappy to let them kiss him, either, but it felt too much like taking advantage of them to say so. Failing to say it didn't change what happened, of course. He was conflicted about who was at fault, here. 

“YOU'RE sorry?” Dean moved his hand only to shoot the angel an incredulous glance, shaking his head. “It's not your fault a few beers turn us into – into a couple dumbasses!” He sputtered the last part, unable to meet Castiel's eyes again. 

This really wasn't the reaction that he'd had expected. 

“Dean, you asked first,” Cas pointed out, leaning on the counter again near him. “And it wasn't unpleasant.” He shrugged, looking down at the kitchen floor. He'd had hours to study the memory of the couch cushions pressed to his back, the feel of Dean's hands on his face, their lips pressed together passionately... He wondered what parts of it Dean could remember clearly. It seemed like it would be difficult to forget.

The click of ceramic on the counter made them both jump. Cas and Dean both glanced over at the coffee maker, finding Sam standing there pouring himself a mug. His hair was a tousled mess, and he looked exhausted. Unlike Dean, he'd apparently changed clothes before bed, because he was wearing a pair of pajama pants and an oversized V-necked shirt with the sleeves pushed up around his elbows. 

Realizing they'd noticed him, the taller man glanced at Dean first, then offered Cas an apologetic smile. 

“Uh...good morning, Cas. Thanks for letting us sleep in.”

“Good morning, Sam.” The angel smiled at him, turning and handing Dean his coffee again. The older brother quickly drank it to avoid having to say anything yet.

Sam cleared his throat, glancing between Dean and Cas several times. 

“A-about last night–“

“You both were drunk, and you both kissed me,” Castiel replied. If he took as long to get to that part of the conversation as Dean had, they would be standing in the kitchen all day. “You asked permission first, though, and you have no reason to apologize.” He added a pointed look to show that he was serious.

Surprised, Sam blinked and mustered a shy smile.

“Okay.” 

“Okay?” Dean finally spoke up, sitting his mug on the counter loudly. The other two glanced quickly at him. “That's it? Okay? 'Oh, no big deal, we were just making out on the couch last night, doesn't change a thing'?” He asked a bit plaintively, freckles framed by his red cheeks. 

Sam shrugged a shoulder, blushing as well.

“It was just a stupid dare, Dean. If Cas is okay with it, so am I.”

Sighing heavily, Dean turned to Castiel. 

“Are you? This isn't totally weird for you? Really?”

“I am perfectly okay, Dean,” the angel assured him, unable to hide how amused he was. Poor Dean. It was only a kiss, but it seemed so threatening to him for some reason. “And Sam and I will keep our promise from last night – we won't tell anyone.” He and the younger brother exchanged a solemn nod to confirm it. 

Dean stood there with his coffee mug in hand, and gave them both a long dubious look. When they didn't say anything else, he finally shook his head and made a beeline for the kitchen door. 

“Alrighty then. Water under the bridge.”

“You sure?” Sam called after him. From his tone, he clearly didn't think Dean was sure.

“Just kissing, no biggie!” Dean called back sarcastically, rounding the corner and disappearing down the hallway.

Cas tilted his head, looking at the empty doorway after he was out of sight. If he didn't know better, he would have thought that Dean's feelings were hurt. The brothers were so different that even their reactions to this were nothing alike. Dean seemed almost bothered that Castiel hadn't blamed him for what happened, like he'd already had it all planned out that it would be his fault. If anyone was at fault, it was Castiel for going along with it. 

“He still seems bothered,” he told Sam.

“Don't worry about it, Cas.” The tall brunette seemed much more at ease than his brother, calm and sipping his coffee, but his face was still flushed as well. Memories of his arms around Castiel's waist and the slow, gentle kiss were enough to distract the angel into a long moment of silence. Sam had admitted that he had kissed men before, so perhaps he was more comfortable with the idea. He'd still been drunk while doing so, though, and he'd said it himself — he thought of it as nothing more than a stupid dare.

It was best not to linger on either kiss for too long.

Sam interrupted the angel's somewhat sad thoughts with a small wince, rubbing his temple with the hand not holding the coffee. “He'll be in a better mood once the hangover's gone, I'm sure,” he continued. “Remind me not to drink the whole liquor store next time, okay?”

Castiel patted his shoulder, smiling for his sake. 

“I'll do that, Sam.”


	3. Longing

Castiel had promised that the kisses hadn’t changed anything between them. At the time, he had meant it. Allowing them to kiss him had been done out of curiosity. Instead of leaving that curiosity satisfied, though, the double dare had left him longing to be kissed again.

Sam and Dean had no idea, he was sure. As far as they knew it was “just a stupid dare,” as Sam had said. It had been three weeks since then, and everyone was doing a great job acting like the kisses hadn’t ever happened. They hadn’t stayed in the bunker and drank together since, though. In fact, though nobody said a word about it, the brothers had avoided drinking again until tonight. Rather than the comfortable quiet of the bunker with the three of them sitting on the couch, though, Dean had insisted that they go to a little bar nearby.

It was loud and crowded in there, with a man and woman playing guitar and singing in one corner, and for once Castiel didn’t want to watch humanity in its various antics. He just wanted to leave.

“You’re quiet, Cas,” Sam commented. The taller man sat beside him at their little table, a beer in his hand. He smiled, but Cas could tell that he was concerned. 

Oh, no. Did he realize?

The angel mustered a smile for his sake as usual, focusing on his own beer in front of him. He’d barely touched it.

“I’m just thinking, Sam.”

Thinking OF Sam, now. Where Dean had been overly cheerful about everything lately, his brother had been extra quiet. Was he studying memories of that night, too? Was it only Castiel who couldn’t stop thinking of it? 

Sam sometimes would sit and read books with him, or make an extra cup of tea and just hand it to Cas with the excuse that he’d make it for everyone, but Dean wouldn’t drink it. Those were gestures of friendship, though. If he had any desire to kiss Castiel again, he wouldn’t have considered the dare something stupid.

Castiel was surprised out of his thoughts by a touch. Sam was patting his shoulder and looking sympathetic.

“I know, I’d rather be at home, too,” he admitted. “Dean’s only here to talk to some waitress — he’s not even hanging out with us.”

He nodded over at the bar. Cas was well aware that Dean was over there chatting up the attractive blond woman near the counter, and had been trying to figure out why that bothered him for awhile now. He glanced when Sam did, though, and saw something that made his breath catch in his throat.

Dean kissed her.

Just like that, he put a hand on her cheek, and she leaned close, and they kissed. 

Cas froze and stared even after the kiss had passed, stunned. They were laughing now, smiling at each other. Why? Why did that feel like a stab in the chest? He should have been happy for Dean, but instead he was remembering those lips pressed to his own. He wished for that again so much that it ached.

“Cas?” Sam had noticed his reaction, and was blinking at him in surprise.

“I…” The angel shook his head and pushed his chair back, abandoning the beer and heading straight out the door. He was confused and hurt, somehow, and he didn’t understand why. It was impossible to hide from Sam, and he could hear the brunette’s quick steps after him as he retreated out the back door of the bar. 

The night air had a crisp edge to it, and the stars and moon shone brightly above. Cas stopped as soon as he was outside, standing near the dumpster just beside the door and wrapping his arms around himself. 

“Hey.” Sam closed the door behind them, turning to him. Castiel could hear the worry in his voice. “Cas, are you okay?”

“I know I said that I was,” the angel said sadly, “but I’m not, Sam. The kisses — I can’t forget them as easily as you and Dean.”

“Oh, the, uh…oh.” Sam definitely sounded surprised. Cas sighed and turned to face him, feeling guilty for making this into more than it was.

“I’m sorry. I know it was only supposed to be a game,” he said, in case that wasn’t clear. Somehow, that only made the ache worse. What would Sam think? How could he explain what he didn’t understand, himself? 

“Cas,” Sam sighed, placing a hand on his shoulder. “Hey, you don’t have to apologize. The whole thing was my idea, remember?” He sounded guilty, too. That was all wrong…this wasn’t his fault, not really.

“The kisses weren’t the problem,” Cas insisted glumly. “I am, Sam. I…I wish that someone would kiss me for real. Not because they were drunk, or because it was a dare, but because they wanted to kiss me.”

Was that really it, though? No, he didn’t want “someone” to kiss him. He wanted Sam and Dean to kiss him again. Him, and not other people. 

That seemed selfish, wishing for both of them. He didn’t want either brother to think he didn’t care for him, though, when there was just as much longing for both of them.

Sam stepped closer, and then his arms were going around the angel’s waist. Cas was surprised at how warm the hug was. Did Sam pity him?

“I’m sorry, Cas. I didn’t mean to make you feel like you’re not important to us,” the taller man said quietly. He got no response. Cas wasn’t sure what to say to that. Of course they hadn’t meant any harm — he was the one putting himself into such a miserable state for taking the dare seriously. 

Sam sighed. 

“I-I meant to do the opposite, okay? I thought Dean had a thing for you, and he might realize it if he kissed you, so…”

Castiel pulled away only enough to look up at him. If Dean hadn’t realized, then Sam was wrong about him. That hurt even more. 

Sam’s hazel eyes were shining in the light from the stars. He looked so pained to be the cause of all of this that Cas could hardly be angry with him. He really didn’t feel angry, just sad. 

“I wasn’t going to say anything,” he whispered, looking down. “You are my friends — family — everything I have on earth, Sam. Both of you.” He pulled away from the hug, turning back toward the street. “I know it isn’t the same from your perspectives. To you, I am not the world — I am an angel.”

“No, you’re OUR angel,” Sam told him, placing both hands on his shoulders. “And we want you here, and…Cas, I’d kiss you because it’s you.”

It would have seemed like an offer only out of sympathy, but Sam sounded moved by what he’d said. He almost sounded tearful.

Castiel turned around reluctantly to face him again, wishing he had managed to hide his reaction to Dean’s antics in the first place. He didn’t want to hurt Sam — that was the last thing that he wanted.

“You don’t have to do that,” he said, mustering a small smile for the brunette’s sake. “Thank you for listening to me, Sam. I feel a little better.” 

Sam looked like he wanted to say more, but he only nodded quietly. It wasn’t a happy conclusion to the conversation, but Castiel didn’t want Sam to kiss him to make him feel better. He wanted a kiss like the one that night on the couch — relaxed, trusting. If Sam didn’t truly want to kiss him, then he didn’t want to be kissed.  


* * *

  
They drove home in the Impala. Dean had left with the waitress by the time Cas and Sam went back inside, and the thought of that was too painful for the angel to spend any more time pretending to enjoy the bar. Sam didn’t want to be there, either; he was definitely bothered by their conversation outside.

He hadn’t said much during the trip home, even, and retreated to his room after only a few minutes. 

Castiel sat alone in the middle of the couch, looking at the wall where Dean had joked they should put a TV. He went over the memories of the kisses in his mind once again — the way neither of them had hesitated at all, except to be sure that he was willing to be kissed. The way each had done it so differently, but with great love from both.

Love? Why did he attach love to something that had been a joke to them? It had felt so genuine at the time. Was he longing for their affection so much that he was embellishing the memories? 

No. He had gone over these details countless times in the past few weeks. He hadn’t ached for anything like this until after the kisses. There must have been something there.

A door opening and closing pulled him from his thoughts. The front door, not Sam’s room.


	4. Do-over

What was Dean doing home so early? It couldn’t have been more than an hour since Sam and Cas had left the bar. Dean was stepping quietly across the main room floor, though, looking around in the lamplight until he spotted the angel on the couch.

“Cas,” he said, squaring his shoulders. “Hey.”

“Hello, Dean,” Castiel replied flatly, going back to looking at the empty wall in front of him. He couldn’t will himself to pretend to be cheerful right now. Dean had left with that woman, and if he was back this fast then they probably hadn’t even gone back to her home before having sex. Just the thought of it hurt him, made him ill. He was frustrated with himself for being so affected. 

Footsteps approached the couch, and he was further annoyed when the green eyed man sat down on the cushion beside his. From the corner of his eye, he saw Dean fidget, clenching his hands into fists and resting them on top of his knees.

“I didn’t go home with her,” he said finally, awkwardly. “Shelby. The, uh, waitress.”

“She seemed happy to do whatever you wished at the bar,” Castiel said evenly, frowning at the wall. Why tell him this?

“I mean nothing happened,” Dean clarified, sounding surprised he’d been paying attention that closely. “I told her I had to go, and she went home. Without me.”

Castiel slowly turned to look at him, feeling that ache in his chest again. No, it was foolish to even hope… He couldn’t help it, though.

Dean’s green eyes avoided his. He blushed, studying the floor in front of the couch, and fidgeted with his hands again before placing them right back where they had rested before. The angel took note of the blushing and blinked, tilting his head.

“Cas, let’s, uh. Let’s talk about a hypothetical situation for a minute, okay?”

Hypothesis about what? Dean was much smarter than he acted, but he rarely used such words in a regular conversation.

Uncertainly, Cas agreed, “Okay.” 

“Let’s say — hypothetically,” Dean began, “That you got drunk and did something you’ve wanted to do for a long time. Now — hypothetically — let’s say you…” He looked at his hands and trailed off, licking his lips. “You wish you didn’t do it while drunk. Hypothetical you wants a do-over. What would you do?”

Castiel stared at him for a long moment. He had to be referring to the kiss, right? …Hypothetically. 

“I would consider why it took alcohol for me to finally do it,” he replied carefully, “and whether there were any other factors. Then, if I still wanted a do-over…I would do it again.”

Dean glanced at him quickly, his face flushing, and he cleared his throat.

“Y-you’d be okay with that?”

Before Cas could reply, the sound of quick footsteps caught their attention.

“Cas, we need to talk. Look, I-I didn’t offer to kiss you back there just because of Dean, I-”

At the abruptly-ended sentence, Dean and Castiel both turned back to find Sam about halfway between the couch and the door. He’d cut himself off when he noticed two people on the couch, it looked like. When his brother turned around, his eyes widened, and he immediately started backpedaling, inching toward the hallway door again.

“Dean. You’re back. Already,” he mumbled, looking anywhere but at the two of them. 

“And you’re awake,” Dean observed, also mumbling. He wouldn’t look at Sam, either.

Castiel would have been awkward, too, if he wasn’t so busy being relieved that they were trying to talk to him about the kisses. Finally. So they HAD both been thinking about them, too.

“Come and sit with us, Sam,” the angel said, beckoning the younger brother toward the couch. Sam started to shake his head, but Castiel insisted, “Please. We should all talk.”

They’d finally slipped up and said something. The last thing he wanted was another three weeks of pretending that this conversation didn’t happen.

Reluctantly, Sam stepped over and sat down on the other side of Castiel, leaving them sitting just like they were the night of the dare. Sam had been cheerful and teasing then, though; now he was tired-eyed, and his hair was a tousled mess. He’d probably tried to sleep and failed.

“Sam. Dean,” Cas began, glancing between them. He didn’t have to look far. As usual, the couch was a bit too small, especially for Sam; they were elbow to elbow. “You may have been intoxicated when you kissed me, but I was not — and I know that’s what this is about.”

“No, it’s about Dean being an idiot,” Sam grumbled, running a hand through his hair. He sighed heavily.

“Hey, I wasn’t THAT drunk,” Dean replied bitterly, crossing his arms. “And the dare was your idea, Sammy.”

“I only did it to make you kiss him already, Dean. You’re not getting any younger.”

Dean’s face turned pink, his freckles standing out brightly, and he sputtered.

“Wh-what makes you so sure I have a thing for Cas? Why do you think that?”

“I don’t know, maybe all the staring and the licking your lips at him all the time?” Sam rolled his eyes.

Dean leaned forward to scowl at him around Castiel. 

“Like you can talk! We all heard you when you got here — you tried to kiss him again, didn’t you? And I’M the one who’s stuck on him?” He gestured to the angel pointedly.

Castiel glanced from him to Sam, trying to press back against the couch so they didn’t have to lean around him. It was probably for the best that somebody was in the middle so they weren’t right next to each other, but he felt like he should mediate in some way. 

Sam’s scowl faltered, and he shook his head. 

“He turned me down, Dean. He likes YOU.” He met Castiel’s eyes briefly, very sadly, before going back to scowling at his brother. “If you weren’t off hitting on waitresses maybe you would’ve noticed!”

Dean opened his mouth to reply, then shut it again, startled into silence.

Cas was startled, too. Sam really hadn’t been offering the kiss only out of pity, then, or apology?

He turned and took one of the taller man’s hands. Before either of them could comment on it, he grabbed one of Dean’s hands as well, holding them tightly. If the brothers saw each other as competition, this was never going to work. He had to reassure them.

“Perhaps I should talk first,” he suggested. 

Sam sighed and nodded. Dean just shrugged. 

Both of them still looked kind of hurt, but also kind of flustered. He could do this — he could fix it. He wasn’t that good at talking to people, but Sam and Dean knew him the best of anybody on earth.

“I’m sorry,” he began, focusing on the floor in front of the couch. “I should have said something about this sooner, but I thought that I was the only one. After you both kissed me, I haven’t been able to stop thinking of it. Of you. I know it was supposed to be just a game, but I-I was not drunk like you.”

“We’re, uh. We’re sorry about that, Cas,” Dean offered, squeezing his hand. “You didn’t have to go along with it.” 

Sam nodded in agreement there.

“No — don’t apologize.” Cas frowned, glancing between them. “I’m saying that I am glad you did it.”

“Yeah, it made Dean kiss you,” Sam agreed halfheartedly. “Finally.” 

“And you, Sam,” Cas said fondly, turning to him. Sam looked so unhappy that he was guilty for turning down the kiss before, even if it had seemed to be the right choice at the time. “I’m sorry I was so vague before. I don’t want ‘someone’ to kiss me — I want you and Dean to kiss me.”

“Him AND me?” Dean was back to sputtering. “What, one of us isn’t good enough for you?”

Castiel kept his eyes on Sam, who still looked quite upset. 

“You’re both good enough, Dean, but I care for both of you. I can’t…” 

“You can’t choose,” Sam supplied for him, sitting up straighter. He glanced quickly at his brother and blushed faintly, hazel eyes searching Cas’s own. “You mean it? If I kissed that waitress, you would’ve stormed out the same as you did with Dean?”

“Stormed — wait, what?” Dean sounded alarmed. Castiel ignored him for the moment, nodding to Sam. 

“I only turned down your offer to kiss me because I didn’t want to be kissed out of pity,” he added, somewhat awkwardly. “I’m sorry, I didn’t realize that you were offering as anything more than a friend, Sam.”

“You were kind of…hung up on the Dean and waitress thing at the time, I guess.” Sam offered a shy, uncertain little smile, and Castiel smiled at him in return. He understood.

Dean wasn’t taking the news nearly so well.

“Cas, what the hell? You STORMED OUT?” He tugged on the angel’s hand to get his attention, and Cas and Sam both turned to him. If Cas had thought that he was blushing before, it was nothing to how his cheeks burned now. “Over me?” He added, voice cracking a little. 

Like that morning with the coffee, he was an endearing mix of flustered and indignant. Sam and his brother really were like night and day. Castiel’s night and day, if they would have him.

“If you were kissing her, I was sure that that meant you didn’t feel anything for me,” Castiel explained, looking down at their clasped hands. Softly, he added, “As I do for you.”

He could almost feel the look exchanged over his head between the brothers. What else could he say? They didn’t seem to understand how he felt. Maybe they thought it was just a physical attraction, since the kisses had been the catalyst for all of this?

Releasing their hands, the angel stood and turned to face them. 

“Sam. Dean,” he said, very seriously. “I love you. I have for a long time, and I thought that just knowing it was enough until you kissed me.”

Sam looked up at him and smiled. He seemed proud of Castiel for being the one to just say it.

Dean, meanwhile, glanced at his brother, then to the angel again. He was back to frowning, but more uncomfortably than angrily now.

“So it’s not just about some stupid drunk dare, then,” he said finally, still blushing. Cas shook his head.

“No.” He looked at Sam, then back to Dean, taking a deep breath. Mustering courage. “If you feel the same, then…I-I would like a do-over. Non-hypothetically.”

Sam and Dean exchanged another glance, and then a small nod. Both brothers held out an arm, inviting him back to the couch. 

Relieved, Castiel sank back down between them and was wrapped in a hug from both sides. Sam’s arm went around his shoulders, Dean’s around his waist, and they sat pressed close to his sides. 

“We love you, too, Cas,” Sam murmured, kissing the top of his head.

“Both of us,” Dean agreed. Not to be outdone by Sam, he kissed the angel’s cheek. “Sorry about the waitress thing…I was only talking to her to try not to think about you.”

Cas looked at him, wondering what to say to that. So that was why Dean hadn’t gone home with her.

He rested his head on Sam’s shoulder, murmuring, “I understand.” 

“So…do-over?”

“Does Sam need to dare you to?”

To his surprise, Dean blushed at the comment. 

“I’ve never kissed a man sober, so…maybe.”

“I dare you to kiss him, Dean,” Sam said drolly, sounding like he was rolling his eyes.

“I’ll do it, but you have to kiss him too,” Dean repeated their words from that night, smiling at Cas. “Double dare. And this time you go first.”

**Notes for the Chapter:**

> THE END
> 
> Thanks for reading my silly, fluffy little fanfic! I love Team Free Will as friends or shipped in various ways, and had a lot of fun writing this. I originally intended for it to just be a one-shot, but Cas had some lingering worries at the end of chapter 1...then at the end of chapter 2...then chapter 3 somehow became a cliffhanger! LOL; I think chapter 4 leaves them at a good point, finally. Anyway, thank you for reading and leaving me those encouraging comments and kudos. I would have probably left it at a one-shot without the requests for a second chapter, so you're all responsible for TFW getting a happy ending this time 'round. =)


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